2-Azido and 2-thiocyanato-2,3-unsaturated ketones were synthesized by utilizing functionalization of 5- or 6-membered cycloalkane-1,2-diones, namely diosphenols, with dimethylthiocarbomoyl chloride, which activates the system towards reaction with nucleophiles in acidic conditions. Replacement of the enolic oxygen of the diosphenols with azide and thiocyanate may be achieved by treating their dimethylthiocarbamates with sodium azide or potassium thiocyanate in boiling acetonitrile/acetic acid.
Azides, thiocyanates, enols, deoxygenation, 1, 2-cyclic diketones
BOZ, MESUT; ZAİM, ÖMER; and ESEN, HİLAL
"A Convenient Synthesis of 2-Azido and 2-Thiocyanato-2,3-Unsaturated Cyclic Ketones,"
Turkish Journal of Chemistry: Vol. 33:
1, Article 6.
Available at: https://journals.tubitak.gov.tr/chem/vol33/iss1/6